This dissertation examines the classical Greek tradition of gynaikokratia (from gynē, woman, and kratos, rule, power) understood as gynocracy, or rule by women, as well as women’s collective use of political power or influence. I contend that ancient figurations of women’s rule express deep anxieties about the most radical aspects of democracy: in particular, the prominence of contentious politics in the democratic polis. Despite women’s political subordination to men, many ancient Greek writers offer imaginations of women’s power (in Greek: gynaikokratia) in their works: they imagine what it might have been like if women, rather than men, had control of the polis. I use the odd figure of women holding political power in the classical context to study how ancient democracy was defined both against and through gendered narratives. My dissertation asks what figurations of women’s rule tell us about the ways in which we think and have thought about politics and political order, especially in relationship to democracy as a regime type. I argue that anxieties related to the possibility of women’s rule, which are fraught with concerns about the consequences of contentious or unruly politics, are at the heart of the most radical aspects of ancient conceptions of democracy. Additionally, this project reads for political community and solidarity created by women. That is, rather than focusing on narratives of individual women in power (i.e., queens), I focus on women’s collectivities, suggesting that depictions of women’s plurality both offer an understanding of gender based on women’s relationships with each other, and cast such an understanding of gender as producing a different account of what it meant to be citizens committed to a political community. Overall, the dissertation tracks how concerns about gynocracy epitomize the most pressing fears and concerns about improper allocations of power (for instance, fears about tyranny of the majority and mob rule). I focus on the association of gynocracy with repertoires of contestation of existing authority that characterized both figures of gynocracy and many descriptions of “radical” democracy in ancient Greek political thought. As I show, figurations of women’s rule over men bear affinity to fears about rule of the lower classes over the aristocracy. Thus, issues of gender and political power depicted in gynocratic texts became central to exploring and renegotiating class relationships and hierarchies within Athenian democracy. That is, in figuring gynocracy through a set of political practices that were characteristic of famously contentious and unruly Athenian “radical” democracy (e.g. excessive freedom, public contestation, unruly political behavior), Greek political commentators cast the latter as feminine, and hence dangerous, hysterical, and uncontrollable.